Down The Rabbit Hole

“Damn! Damn! Damn! Every year he forgot. Well, no. He never forgot. He just put the memories away like old silverware that you didn’t want to tarnish. And every year they came back, sharp and sparkling, and stabbed him in the heart. And today, of all days...”

For anyone who's confused today, I won't spoil/explain what the 25th of May is in the Discworld fandom, because I think a big part of what's special about it is the way the plot unfolds in the book.

What I will explain though is that it'll make sense when you reach a book called Night Watch, which is the 29th book in the overall series and the 6th book in the City Watch subseries. If you haven't got that far yet, just take your time and enjoy the series! If you want to start with the City Watch stories then the first book you should check out is Guards! Guards!

See, part of the conceit of the PotC trilogy is that all myths are true. Nearly every supernatural element in the franchise has a root in some real world mythology or pirate lore, although some of them are mashed together.

Another thing is that they take place at the end of the Golden Age of Piracy, and the more the map gets filled in, and the more the Royal Navy takes power, there less room there is for the mystical and supernatural in the world. This is explicitly called out in At World's End with the death of the kraken:

Barbossa: The world used to be a bigger place. Jack: The world's still the same. There's just... less in it.

The only way to access the world of the supernatural is through the supernatural itself. You can only get to the Isla de Muerta with Jack's compass that points to whatever you desire, or if you already know where its is. You need Tia Dalma's map to find the edge of the world. To access the supernatural, you need to already be immersed in it.

When we go to Tortuga (or any pirate controlled space) we leave behind the sensibilities of the real world and enter this bizarre perpetual revel of debauchery and violence that could never sustain itself in a world bound by sense.

That makes Jack our Puck character, a trickster of tricksters who can invert your fortunes just by letting him talk to you.